US6713598B2 - Method to make a solid polymeric phosphate and resinous compositions containing it - Google Patents

Method to make a solid polymeric phosphate and resinous compositions containing it Download PDF

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Publication number
US6713598B2
US6713598B2 US10/229,836 US22983602A US6713598B2 US 6713598 B2 US6713598 B2 US 6713598B2 US 22983602 A US22983602 A US 22983602A US 6713598 B2 US6713598 B2 US 6713598B2
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bis
hydroxyphenyl
compound
reaction
group
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US10/229,836
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US20040044134A1 (en
Inventor
Immanuel I. Selvaraj
Gerrit de Wit
Jan Gosens
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SHPP Global Technologies BV
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General Electric Co
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Priority to DE60305251T priority patent/DE60305251T2/de
Priority to JP2003302332A priority patent/JP2004131715A/ja
Priority to EP03255311A priority patent/EP1394192B1/en
Publication of US20040044134A1 publication Critical patent/US20040044134A1/en
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Assigned to SABIC INNOVATIVE PLASTICS IP B.V. reassignment SABIC INNOVATIVE PLASTICS IP B.V. ASSIGNMENT OF ASSIGNORS INTEREST (SEE DOCUMENT FOR DETAILS). Assignors: GENERAL ELECTRIC COMPANY
Assigned to CITIBANK, N.A., AS COLLATERAL AGENT reassignment CITIBANK, N.A., AS COLLATERAL AGENT SECURITY AGREEMENT Assignors: SABIC INNOVATIVE PLASTICS IP B.V.
Assigned to SABIC INNOVATIVE PLASTICS IP B.V. reassignment SABIC INNOVATIVE PLASTICS IP B.V. RELEASE OF SECURITY INTEREST Assignors: CITIBANK, N.A.
Assigned to SHPP GLOBAL TECHNOLOGIES B.V. reassignment SHPP GLOBAL TECHNOLOGIES B.V. ASSIGNMENT OF ASSIGNORS INTEREST (SEE DOCUMENT FOR DETAILS). Assignors: SABIC GLOBAL TECHNOLOGIES B.V.
Assigned to SABIC GLOBAL TECHNOLOGIES B.V. reassignment SABIC GLOBAL TECHNOLOGIES B.V. CHANGE OF NAME (SEE DOCUMENT FOR DETAILS). Assignors: SABIC INNOVATIVE PLASTICS IP B.V.
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    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G79/00—Macromolecular compounds obtained by reactions forming a linkage containing atoms other than silicon, sulfur, nitrogen, oxygen, and carbon with or without the latter elements in the main chain of the macromolecule
    • C08G79/02—Macromolecular compounds obtained by reactions forming a linkage containing atoms other than silicon, sulfur, nitrogen, oxygen, and carbon with or without the latter elements in the main chain of the macromolecule a linkage containing phosphorus
    • C08G79/04—Phosphorus linked to oxygen or to oxygen and carbon
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
    • C09K21/00—Fireproofing materials
    • C09K21/06—Organic materials
    • C09K21/12—Organic materials containing phosphorus

Definitions

  • a solid polymeric phosphate can be prepared by a multi-step process.
  • a phosphorus oxyhalide is reacted with a monohydroxyaromatic compound to form a monoaryldihalophosphate.
  • the phosphorus oxyhalide comprises at least one of phosphorus oxychloride or phosphorus oxybromide.
  • the phosphorus oxyhalide comprises phosphorus oxychloride.
  • the amount of phosphorus oxyhalide required can range from about 1 to about 5 times the amount that is stoichiometrically required to complete the reaction with the monohydroxyaromatic compound.
  • the molar ratio of phosphorus oxyhalide to monohydroxyaromatic compound which can be used in the present method can in one embodiment be about 1:1, in another embodiment about 2:1, in another embodiment about 3:1, in another embodiment about 4:1, and in still another embodiment about 5:1. In some embodiments, the molar ratio of phosphorus oxyhalide to monohydroxyaromatic compound is greater than about 1:1.
  • the reaction is performed at a temperature suitable for the monohydroxyaromatic compound to react with the phosphorus oxyhalide.
  • monohydroxyaromatic compounds with ortho substituents may require a higher temperature than those with para or meta substituents.
  • the temperature range for reacting monohydroxyaromatic compound with phosphorus oxyhalide is between about 100° C. and 200° C.
  • the reaction temperature may be held in the desired range for a sufficient period of time such that essentially all the monohydroxyaromatic compound in the reaction mixture has reacted.
  • Analytical methods for monitoring the concentration of monohydroxyaromatic compound in the reaction mixture are well known to those skilled in the art, and may be applied as appropriate depending upon the degree of accuracy desired.
  • the total reaction time of monohydroxyaromatic compound with phosphorus oxyhalide is in a range of between about 1 hour and about 18 hours. In still another particular embodiment, the total reaction time of monohydroxyaromatic compound with phosphorus oxyhalide is in a range of between about 10 hours and about 16 hours. In various embodiments, the acidic components of the reaction may be removed by bubbling these into alkaline solutions.
  • the product of the first reaction is reacted with at least one dihydroxyaromatic compound.
  • the reaction may be conducted by any convenient means. In some embodiments the reaction is conducted in solution, while in other embodiments the reaction is conducted in the melt in the absence of solvent. At least one acid acceptor or at least one catalyst, or a combination of acid acceptor and catalyst may be present in some embodiments of the second step of the method.
  • the reaction mixture following complete addition of organic solution of the first reaction product (or its purified equivalent) to a solution comprising a dihydroxyaromatic compound is treated with a monohydroxyaromatic compound to serve as a chain-stopper for the polymer product.
  • Suitable monohydroxyaromatic chain-stoppers include those monohydroxyaromatic compounds disclosed hereinabove. Additional acid acceptor may be added before, simultaneous with, or after said addition of monohydroxyaromatic chain-stopper. The amount of added chain-stopper may be readily calculated by those skilled in the art to provide any desired degree of chain-stopped polymer of any desired molecular weight.
  • dihydroxyaromatic compounds include: 2,2-bis-(4-hydroxyphenyl)-butane; 2,2-bis-(4-hydroxyphenyl)-2-methylbutane; 1,1-bis-(4-hydroxyphenyl)-cyclohexane; bis-(4-hydroxyphenyl); bis-(4-hydroxyphenyl)-sulphide; 2-(3-methyl-4-hydroxyphenyl-2-(4-hydroxyphenyl)-propane; 2-(3,5-dimethyl-4-hydroxyphenyl)-2-(4-hydroxyphenyl)-propane; 2-(3-methyl-4-hydroxyphenyl)-2-(3,5-dimethyl-4-hydroxyphenyl)-propane; bis-(3,5-dimethylphenyl-4-hydroxyphenyl)methane; 1,1-bis-(3,5-dimethylphenyl-4-hydroxyphenyl)ethane; 2,2-bis-(3,5-dimethylphenyl-4-hydroxyphenyl)propan
  • n is an integer greater than or equal to about 2; and Ar is a residue derived from a monohydroxyarornatic compound.
  • substantially free of radicals of halogen bound to phosphorus means that in one embodiment, less than about 500 ppm of such species can be detected; in another embodiment, less than about 100 ppm of such species can be detected; in another embodiment, less than about 50 ppm of such species can be detected; in another embodiment, less than about 20 ppm of such species can be detected, and in another embodiment, less than about 10 ppm of such species can be detected.
  • substantially free of radicals of halogen bound to phosphorus means that none can be detected using the chosen analytical method.

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Health & Medical Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Medicinal Chemistry (AREA)
  • Polymers & Plastics (AREA)
  • Engineering & Computer Science (AREA)
  • Materials Engineering (AREA)
  • Compositions Of Macromolecular Compounds (AREA)
  • Polymers With Sulfur, Phosphorus Or Metals In The Main Chain (AREA)
  • Fireproofing Substances (AREA)
US10/229,836 2002-08-28 2002-08-28 Method to make a solid polymeric phosphate and resinous compositions containing it Expired - Lifetime US6713598B2 (en)

Priority Applications (4)

Application Number Priority Date Filing Date Title
US10/229,836 US6713598B2 (en) 2002-08-28 2002-08-28 Method to make a solid polymeric phosphate and resinous compositions containing it
DE60305251T DE60305251T2 (de) 2002-08-28 2003-08-27 Verfahren zur Herstellung von einem festen polymeren Phosphat
JP2003302332A JP2004131715A (ja) 2002-08-28 2003-08-27 固体ポリマー状ホスフェートの製造方法及び該ホスフェートを含む樹脂組成物
EP03255311A EP1394192B1 (en) 2002-08-28 2003-08-27 Method for the preparation of a solid polymeric phosphate

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
US10/229,836 US6713598B2 (en) 2002-08-28 2002-08-28 Method to make a solid polymeric phosphate and resinous compositions containing it

Publications (2)

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US20040044134A1 US20040044134A1 (en) 2004-03-04
US6713598B2 true US6713598B2 (en) 2004-03-30

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US (1) US6713598B2 (enExample)
EP (1) EP1394192B1 (enExample)
JP (1) JP2004131715A (enExample)
DE (1) DE60305251T2 (enExample)

Cited By (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN102276874A (zh) * 2011-05-11 2011-12-14 华南理工大学 一种主链含磷硅硼低聚物阻燃剂及其制备方法
US9969881B2 (en) 2014-07-18 2018-05-15 Carolina Color Corporation Process and composition for well-dispersed, highly loaded color masterbatch
US10428189B2 (en) 2014-07-18 2019-10-01 Chroma Color Corporation Process and composition for well dispersed, highly loaded color masterbatch

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* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPWO2005004563A1 (ja) * 2003-07-03 2006-08-24 株式会社日立製作所 モジュール装置及びその製造方法
WO2008016632A1 (en) * 2006-08-01 2008-02-07 University Of Massachusetts Deoxybenzoin-based anti-flammable polyphosphonate and poly(arylate-phosphonate) copolymer compounds, compositions and related methods of use
JP5927883B2 (ja) * 2011-12-09 2016-06-01 三菱瓦斯化学株式会社 熱可塑性樹脂組成物
KR20140080360A (ko) * 2012-12-20 2014-06-30 제일모직주식회사 인계 공중합체, 이의 제조방법 및 이를 포함하는 난연성 열가소성 수지 조성물
CN112961363A (zh) * 2020-10-29 2021-06-15 广东广山新材料股份有限公司 一种聚合型磷硅协同阻燃剂及其制备方法和应用
CN113402715A (zh) * 2020-11-06 2021-09-17 江苏集萃先进高分子材料研究所有限公司 一种新型磷氮阻燃剂及其制备方法
CN113929864B (zh) * 2021-11-20 2023-03-24 扬州工业职业技术学院 一种阻燃保温型聚氨酯材料
CN114075239A (zh) * 2022-01-07 2022-02-22 山东旭锐新材有限公司 一种bdp阻燃剂的制备方法

Citations (12)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2616873A (en) 1948-03-23 1952-11-04 Gen Electric Organo-phosphorus resinous compositions
US2636876A (en) 1948-01-02 1953-04-28 Ici Ltd Preparation of resinous aromatic polyphosphates
US3028365A (en) 1953-10-16 1962-04-03 Bayer Ag Thermoplastic aromatic polycarbonates and their manufacture
US3148172A (en) 1956-07-19 1964-09-08 Gen Electric Polycarbonates of dihydroxyaryl ethers
US3271367A (en) 1955-03-26 1966-09-06 Bayer Ag Thermoplastic polycarbonates of dihydroxydiarylene sulfones and their preparation
US3271368A (en) 1963-05-02 1966-09-06 Borg Warner Sulfonate-thiocarbonate copolymers
US4217438A (en) 1978-12-15 1980-08-12 General Electric Company Polycarbonate transesterification process
US4481338A (en) 1982-09-10 1984-11-06 Bayer Aktiengesellschaft Flame-resistant polymer mixtures
US4482693A (en) 1982-09-10 1984-11-13 Bayer Aktiengesellschaft Polyphosphates and the production thereof
US5728859A (en) 1996-10-31 1998-03-17 Akzo Nobel N.V. Process for making monohydroxy-terminated phosphate compositions
US5750756A (en) 1994-11-01 1998-05-12 Akzo Nobel Nv Process for the formation of hydrocarbyl bis(hydrocarbyl phosphate)
JP2000239544A (ja) 1998-12-24 2000-09-05 Asahi Chem Ind Co Ltd 難燃性樹脂組成物

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US3987008A (en) * 1971-12-17 1976-10-19 Celanese Corporation Flame retardant polyester
JPS63227632A (ja) * 1987-03-17 1988-09-21 Daihachi Kagaku Kogyosho:Kk 難燃剤の製造方法
JP3199844B2 (ja) * 1991-06-14 2001-08-20 エチル・ペトロリアム・アデイテイブズ・インコーポレーテツド 有機ホスフエート類およびそれらの製造
US5457221A (en) * 1993-03-03 1995-10-10 Akzo Nobel N.V. Process for the manufacture of poly (hydrocarbylene aryl phosphate) compositions

Patent Citations (12)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2636876A (en) 1948-01-02 1953-04-28 Ici Ltd Preparation of resinous aromatic polyphosphates
US2616873A (en) 1948-03-23 1952-11-04 Gen Electric Organo-phosphorus resinous compositions
US3028365A (en) 1953-10-16 1962-04-03 Bayer Ag Thermoplastic aromatic polycarbonates and their manufacture
US3271367A (en) 1955-03-26 1966-09-06 Bayer Ag Thermoplastic polycarbonates of dihydroxydiarylene sulfones and their preparation
US3148172A (en) 1956-07-19 1964-09-08 Gen Electric Polycarbonates of dihydroxyaryl ethers
US3271368A (en) 1963-05-02 1966-09-06 Borg Warner Sulfonate-thiocarbonate copolymers
US4217438A (en) 1978-12-15 1980-08-12 General Electric Company Polycarbonate transesterification process
US4481338A (en) 1982-09-10 1984-11-06 Bayer Aktiengesellschaft Flame-resistant polymer mixtures
US4482693A (en) 1982-09-10 1984-11-13 Bayer Aktiengesellschaft Polyphosphates and the production thereof
US5750756A (en) 1994-11-01 1998-05-12 Akzo Nobel Nv Process for the formation of hydrocarbyl bis(hydrocarbyl phosphate)
US5728859A (en) 1996-10-31 1998-03-17 Akzo Nobel N.V. Process for making monohydroxy-terminated phosphate compositions
JP2000239544A (ja) 1998-12-24 2000-09-05 Asahi Chem Ind Co Ltd 難燃性樹脂組成物

Non-Patent Citations (2)

* Cited by examiner, † Cited by third party
Title
Chapter 35-Noncondensed Aromatic Compounds, p. 5553, paragraphs c-e, E. Wieckowski, (1963).
Ki-Soo Kim, "Phosphorus-Containing Polymers. I. Low Temperature Polycondensation of Phenylphosphonic Dichloride with Bisphenols", Journal of Applied Polymer Science, vol. 28, pp. 1119-1123, (1983).

Cited By (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN102276874A (zh) * 2011-05-11 2011-12-14 华南理工大学 一种主链含磷硅硼低聚物阻燃剂及其制备方法
CN102276874B (zh) * 2011-05-11 2012-07-18 华南理工大学 一种主链含磷硅硼低聚物阻燃剂及其制备方法
US9969881B2 (en) 2014-07-18 2018-05-15 Carolina Color Corporation Process and composition for well-dispersed, highly loaded color masterbatch
US10428189B2 (en) 2014-07-18 2019-10-01 Chroma Color Corporation Process and composition for well dispersed, highly loaded color masterbatch

Also Published As

Publication number Publication date
US20040044134A1 (en) 2004-03-04
DE60305251D1 (de) 2006-06-22
EP1394192B1 (en) 2006-05-17
DE60305251T2 (de) 2007-02-15
JP2004131715A (ja) 2004-04-30
EP1394192A1 (en) 2004-03-03

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